Should I consider a remote co-founder? What experiences have you had - good or bad?
There are circumstances where it can work fine, and my situation just happened to be one of those circumstances. I think the following has to be true for it to work extremely well:
1. Very clear boundary between your job and your co-founders job. If you need to touch the same files in your codebase more than once or twice a week, you're probably working on stuff that is too closely related. In my case, the software was my co-founders job, and everything else (including some UI work, but mainly the website to sell the product, the business-related paperwork and banking/taxes minutiae, marketing, documentation, etc.) was mine.
2. A good working relationship, where you both understand the others goals and understand what aspects of the task are to be done by each of you. Some sort of task management tool--we've used a bug tracker heavily from the very earliest days of the company--helps here.
3. Equal dedication to the goal. Since you aren't in the same room very often, it can be hard to be sure that everybody is doing their part. And if everyone isn't "firing on all cylinders" for the good of the company, it will fail.
But, you should keep in mind that the vast majority of Open Source projects are built and run by people who meet maybe once or twice per year. I worked for years on the Squid project and only ever met two of them in person (there are about 5 long-time core developers on the project) and spoke to a couple of others on the phone a few times. It doesn't stop them from getting great things done. MySQL AB was a famously distributed company--they had developers all over the world. If being acquired for $500M isn't a great success story, I don't know what is.
Though, I should also fess up to the fact that my co-founder and I now both live in the valley, a ten minute drive away, and we get together once a week for status meetings. We're still pretty distributed though...most of our peers that I've met out here work in the same office or in the same apartment. I don't know that I'd be more productive in such a circumstance, or that we'd be further along in our plans...but maybe.
- Inability to brainstorm at any moment
- Weakened brainstorming - It's just not the same via video, IM, or phone
- Paperwork takes longer - Often you both have to sign it. Mailing that crap is just horrendous
- Harder to keep on task - Having each other to keep pushing each other and set tasks and to-do lists is vital
- Meeting with investors is a pain when coordinating two different travel plans
- You just don't get to interact with your co-founders enough to REALLY know whether you're compatible for working together on a startup. You're going to have to be at the same place later on, might as well be now so you know this partnership is going to work 100%
The geographic distance was one of the big factors that killed our startup. Don't do it if you can avoid it in any way.
Inability to brainstorm at any moment? Hardly. Chat is reasonable for this task.
Weakened brainstorming? Maybe. But you can always get together now and then in physical space. We do this every few months if possible.
Paperwork? Um, fax machines, scanners and pdfs. It takes the same amount of time.
Meeting pain? You still have to coordinate both schedules. This is work aroundable.
Motivation and keeping on task? This is a function of personality. It's very true that not everyone can work well virtually. I've found several winners in this regard, but I have also had to fire some people who might have been great in person, but just couldn't cut it remotely.
There are many benefits to working virtually. The talent pool is _much_ larger when it is national or international. The hours are better for everyone. One of my co-workers travels all over surfing in the mornings and working the rest of the day. All your communication (assuming you aren't using the phone much) is logged and can be searched, which is quite handy for those brainstorming sessions. It forces you into decent dev practices and into good communication.
It's not for everyone, surely, but neither is working in an office with your co-workers.
I second each of Mystalic's points, with a single addition: motivation. Everyone -- even startup founders -- needs motivated now and again. When you need it your co-founder will be little help. And (what's much, much worse) when your co-founder needs it your attempts will likely be in vain. Motivation, passion, drive... it's hard enough to sustain those things in a physical setting. Trying to do so in a virtual setting is near-impossible.
I should add a caveat: Motivation is almost never an issue in the beginning, which is why this is such a precarious problem. You'll be tempted to disregard the likelihood for issues down the road in light of the current, rosy status quo. Fact is it's when you hit the dip (like when you miss your first deadline) that things turn sour. Just hope you don't find yourself there without recourse.
My advice is that if you think you absolutely have to found a company with someone in a different geographic region, ask yourself if that's really the case. Chew on it for a night (or a few weeks) if you need to. Err on the side of working with a local co-founder, and if you must work with someone in a different geographic region, move forward with caution.
However, he was also my best friend that I'd known for 10 years.
Remote is fine, but you need to know the person well in real life, or else there will be many, many miscommunications.
I've also worked a few years telecommuting myself, so I've learned a lot of the tricks to maximize the efficiency of that sort of situation. Using things like Jing, GoToMeeting, daily phone status meetings, and, lately, Chatterous, have helped us keep the communication efficiency high for our startup.
Definitely not for everyone, but it can work pretty well if you try hard.
If it is somebody you have worked with and know well, it may not matter if they are in a different time zone, but if you have to ask: it probably will.
IMO productivity in a team, where the people are working on the same thing (which makes DHH's case irrelevant) goes exponentially down with distance. Measuring the distance in feet vs. miles makes more difference than measuring it in miles vs. thousands of miles.
It probably depends on how self-motivated you both are and if you are keeping day jobs. The biggest challenge I've seen is keeping momentum-- and either distance or outside responsibilities are often huge drags -- but only you can make the call ultimately. You could try going long distance with just clear terms laid out so that in three months if stuff isn't getting done you aren't stuck in a lousy partnership.
For the first 6 months we worked remotely, and for the last 3 weeks we've been in the same location. And honestly, the amount of productivity that exists being in the same place at this early stage is not achievable remotely.
1 week same location = 4 weeks remotely (In my opinion)
But I am new to this game, so I cant tell you the otherside of the story.